Red Ryan: Canada’s Fake Reformed Gangster

Red Ryan: Canada’s Fake Reformed Gangster

From Canada is Boring by Jesse Harley, Rhys Waters

May 11, 2026 · 38 min · Episode 516

About this episode

Rhys and Jesse explore the chaotic life of Red Ryan, a notorious Canadian criminal known for his elaborate scams and violent end.

Rhys and Jesse dive into the wild life of Red Ryan, a Toronto-born hooligan who grew into one of Canada’s most notorious early 20th‑century criminals. From leading street gangs at 10, to hard labor in Kingston Penitentiary, to a wartime desertion and a “most daring” prison break that even inspired Ernest Hemingway, Ryan’s story is packed with chaos. They unpack how Ryan pulled off a decade‑long scam as a “reformed” model prisoner—writing a book, sculpting Virgin Mary statues, charming a prison chaplain, and emerging as a media darling with his own radio show—while secretly robbing banks on the side. It all ends in a bloody liquor store shootout in Sarnia that shocks a country that thought it had found its redemption poster boy. Plus, in the STD (Small Talk Dimension) zone, Jesse recounts a ridiculously elaborate 1745 powdered‑wig dinner party, complete with questionable Scottish accents, Jacobite plotting, and a near “diplomatic incident” over a misunderstood signature. For premium content, socials, merch, to leave a voicemail or message us go to canadaisboring.com Hosted on Acast. See acast.com/privacy for more information.

People in this episode

Hosts: Rhys, Jesse

Topics covered

  • crime
  • history
  • Canada
  • gangsters
  • prison
  • media

Keywords

  • Red Ryan
  • Canada
  • gangster
  • prison break
  • crime history
  • Ernest Hemingway
  • liquor store shootout

Mentioned in this episode

Books & works: book, radio show, Virgin Mary statues

Places: Toronto, Kingston Penitentiary, Sarnia

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